(S)-2-[(1R,2R,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-4-methylene-pentanedioic acid di-tert-butyl ester | 686287-66-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-[(1R,2R,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-4-methylene-pentanedioic acid di-tert-butyl ester
• 英文别名: ditert-butyl (2S)-2-[[(1R,2R,5R)-2-hydroxy-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanylidene]amino]-4-methylidenepentanedioate
• CAS: 686287-66-1
• 化学式: C₂₄H₃₉NO₅
• 分子量: 421.577
• InChiKey: ZOWMVUKTHHYDBN-JDVWUOGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  85.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-[(1R,2R,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-4-methylene-pentanedioic acid di-tert-butyl ester 在 柠檬酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 120.0h， 生成 [(4S)-5-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonyl]-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentyl]-phenylphosphinic acid
  参考文献：
  名称：

  Enantioselective synthesis of new 4-substituted glutamic acid derivatives

  摘要：

  Several new 4-substituted glutamic acid derivatives are described: 4-phosphinomethyl glutamic acid derivatives were prepared starting from (2S)-N-Boc-tert-butyl-4-methylene glutamate. The 4-carboxymethyl and 4-aminomethyl glutamic acid derivatives were obtained using asymmetric 1,4-addition conjugate of the enolate of Schiff base I to unsaturated esters. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.006
• 作为产物：
  描述：

  tert-butyl 2-(bromomethyl)acrylate 、 1,1-dimethylethyl N-[(1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylidene]glycinate 在 甲基溴化镁 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 为溶剂， 反应 22.5h， 以72%的产率得到(S)-2-[(1R,2R,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-4-methylene-pentanedioic acid di-tert-butyl ester
  参考文献：
  名称：

  Enantioselective synthesis of new 4-substituted glutamic acid derivatives

  摘要：

  Several new 4-substituted glutamic acid derivatives are described: 4-phosphinomethyl glutamic acid derivatives were prepared starting from (2S)-N-Boc-tert-butyl-4-methylene glutamate. The 4-carboxymethyl and 4-aminomethyl glutamic acid derivatives were obtained using asymmetric 1,4-addition conjugate of the enolate of Schiff base I to unsaturated esters. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.006

文献信息

• Enantioselective synthesis of new 4-substituted glutamic acid derivatives
  作者：Johny Wehbe、Valérie Rolland、Alain Fruchier、Marie-Louise Roumestant、Jean Martinez

  DOI：10.1016/j.tetasy.2004.01.006

  日期：2004.3

  Several new 4-substituted glutamic acid derivatives are described: 4-phosphinomethyl glutamic acid derivatives were prepared starting from (2S)-N-Boc-tert-butyl-4-methylene glutamate. The 4-carboxymethyl and 4-aminomethyl glutamic acid derivatives were obtained using asymmetric 1,4-addition conjugate of the enolate of Schiff base I to unsaturated esters. (C) 2004 Elsevier Ltd. All rights reserved.